1-Iodopropane → 5-(allyl-amino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 327485Notes

Reaction equation

HRID 327485 reaction equation
I[CH2:2][CH2:3][CH3:4].[NH2:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2.Cl.Cl.Br[C:22]1[CH:23]=C2C(=C([N+]([O-])=O)[CH:31]=1)NCC(N)C2>C(OCC)(=O)C>[CH2:2]([N:5]([CH2:23][CH:22]=[CH2:31])[CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2)[CH:3]=[CH2:4].[CH2:2]([NH:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2)[CH:3]=[CH2:4]

Participants

6

Reactant 3

HCID 336431-IodopropaneHCID 159377665-Amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 199193576-Bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride

Product 2

HCID 157450055-(allyl-amino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 157450065-Diallylamino-5,6-dihydro-1H,4H-imidazo[4,5,1-ij]quinolin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure of Example 54, but substituting allyl bromide for iodopropane and 5-(amino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one for 6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine dihydrochloride there were obtained 5-(diallylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one, mp 150-152 from ethyl acetate and 5-(allylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one. The latter compound was converted to the hydrochloride salt, mp 260° from methanol:ether.

Sources & evidence

ORD record
ord-252df3ad80a2416db7fa9ba61eda48f4
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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